


Weather or Not

by FandomPanda_42



Category: Supernatural
Genre: Alternate Universe - College/University, Author doesn't really know how to tag this one fyi, Autistic Castiel (Supernatural), Bisexual Dean Winchester, But not really college-y, Ctrl+V No. 3, Destiel - Freeform, Gay Castiel (Supernatural), M/M, Sex, THIS IS A WIP, Trans Castiel (Supernatural), Will try best, just so you know, transgender male
Language: English
Status: In-Progress
Published: 2021-01-25
Updated: 2021-01-30
Packaged: 2021-03-17 04:34:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 7,692
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28968390
Author URL: https://archiveofourown.org/users/FandomPanda_42/pseuds/FandomPanda_42
Summary: Dean had waited for months to meet his new roommate. A few months before, he applied to colleges, going with Texas A&M. Dean's whole life got turned upside down when he met the gorgeous meteorology major.(I am trying to get better at summaries, please bear with me.)
Relationships: Castiel/Dean Winchester
Comments: 1
Kudos: 9





	1. Intro to College

**Author's Note:**

> This is going to be my first WIP. I have almost thirty others, so I am trying to finish one before moving on. I hope you like it.
> 
> -Corey

Dean awoke to the sound of the door being unlocked, jarred awake from a good rest, but sure enough ready to go. He hopped off his bed and tried to tidy everything as much as he could.

It was finally a few months after he started to talk to his new roommate. He went through the process of applying and getting accepted to Texas A&M, then he started going through the names and descriptions of potential roommates for Hullabaloo Hall.

Dean's bio pretty much said: "Name: Dean/ Age: 18/ Gender: Male/ Description: Howdy, my name's Dean! I'm going to major in psychology. I'm from Austin, Texas. I love to talk about food and cars, but also some nerdy things."

He looked at several different ones, and just not feeling it. He was about to give up, but a specific one caught his eyes: "Name: Castiel/ Age: 18/ Gender: Male/ Description: Uh, hi? My name is Castiel. I want to major in meteorology. I like guinea pigs? But I also like cats, too. My favorite food is a great cheeseburger that I have yet to find. My favorite color is a specific shade of dark blue. I really like smoothies and shakes. I don't know how much I am supposed to say? Should I just stop here? Okay."

Dean laughed for a few moments when he had read that. So, he started talking to the guy. They hit it off quickly and began to talk almost all the time, ready to meet each other. They decided to get a dorm connected to one bathroom, just the two, giving them more space to know each other.

And that brings him back to now. He took a deep breath and put an honest smile on his face when the door opened.

An older, short dude walked in dragging two suitcases, a heavy tote on each arm. He glanced around before his eyes fell on Dean. He pivoted his body to the door and called, "Hey, baby bro, don't be scared! He seems nice!"

A muffled response came back of, "He could still be an ax murderer that wants to tie me to my bed and eat my non-existent limbs.  _ Piece. By. Piece!"  _

Dean chuckled when he heard a deep rumble that he could only assume belonged to Cas.

"Cas, s'alright!" Dean yelled back into the hall. "It's me, Dean! We've only talked for almost every hour of every day!"

There was a crash in the hall, a muffled  _ "dammit"  _ coming shortly afterward. The older dude dropped his bags and ran back into the hall. Dean followed hurriedly.

A few yards from the door, on the floor, was a gangly teenager, his face planted into the floor, dark ruffled hair in an array of madness. Another suitcase was lying nearby, two blankets under him, and the guy himself sprawled out like a starfish.

"That's what you get for having so much shit, baby bro," the older man smirked as he came to help him off the floor. He was eventually helped up, his hands coming down to smooth out his baggy clothes. Dean came to help pick up the suitcase to take back to their dorm room.

He figured that maybe the guy might have been nervous, so he decided to talk. "My parents dropped me off yesterday, I'm glad that now I have someone other than myself to talk to for once. How was the drive from NASA?" One of the things he learned from Cas was that he lived in League City, which was only ten minutes from Johnson Space Center. Dean had never been, but he hoped that one day he and Cas could go together. And yeah, he may or may not have started to like Cas the more he talked to him. Seeing him in person just made him want to hug him and never let go.

Cas looked up at him with a big, poofy, dark blue blanket, and a smaller light blue one. Their eyes connected once before he looked away, down at his blankets, and started to walk to their room.

Once the three of them put everything down, the older man turned to Cas, and said, "How about you go get those last remaining things from the car? I'll help you get situated when you get back. Then, we could see if Dean here would like to have dinner with us? Something we could all agree on?" Cas shifted from foot to foot awkwardly, then nodded once and left, the door shutting on the way out.

The man turned to him intimidatedly. "Okay, Dean. I've got a few short moments to unpack a lot of things on you."

"Uhhh... alright?"

"My name's Gabriel, Castiel's older brother," he jovially said and held out his hand. Dean shook it before Gabriel pulled his back to say more. "I'm going to say some things that I think he never told you. Which, there are a few things that he has to tell you in his own time if he trusts you enough. And it kinda seems he already does. But just give him some time to unwind, okay?" Without waiting for Dean's response, he moved on. "I'm twelve years older than him, making me the perfect age of thirty. I've been his primary caregiver since he was twelve. That was the same year that he was diagnosed with autism- specifically Asperger's. He's also got anxiety and AD/HD. He's on medicine for all of those, so if you see him take stuff several times a day, that's what it's for.

"Our parents had a shitload of money and loved to spend it on us- they still give us the money we need- not that we need it. His special needs were one of the things that sent us packing. We grew up in a hardcore Christian family. They never understood him like I did. One of the other things was that he came out as gay. Man," he chuckled. "That kid knew what he wanted when he was  _ twelve _ . There's also one more thing that did it, but that's the thing that I told you that you can't push him about if you find out. If you need help with anything, here's my personal cell." Gabriel handed him a yellow sticky note with a phone number scribbled down on it. "He's had tons of therapy, so he should be good. But it's a 'just in case' thing."

Dean nodded after processing all of that.

So. His roommate- who might possibly be his best friend- had special needs. He was going to search for everything he could about those to learn to help Cas. He'd do anything to make him more comfortable.

The door opened and Cas entered with a few more tote bags, filled with... stuffed animals?

Yeah, this dude seemed awesome.

That day ended a bit late, Gabriel waving them off and telling them that he'd check on Cas soon.

The finished product of their room was... amazing. Dean's side was forest green with textbooks aligned on the bookshelf. His comforter and sheets matched his filing decorations. Cas's side was a deep blue with touches of a lighter blue. On top of his bed were several dragon plushies, all of different sizes and colors.

Even though Dean thought it was fine for both of them to change in the same room since they were both guys, Cas stiffly shook his head and entered the bathroom with a large sweatshirt and baggy pants, a few more things wadded up in the bundle.

Dean shrugged and finished changing, hopping into bed and telling Cas that he was done.


	2. Lovin' Every Minute Of It

**Notes for the Chapter:**

> Just so you know, this was written by someone who is autistic so the whole 'SQUIRREL!' thing seems common enough in what I write. I'm trying to notice it when I can. 
> 
> This is tagged as M/M, but Cas hasn't had any surgery, so if you're not okay with Cas not being fully male and he and Dean having sex, this might be where you want to go your separate way. (FYI, I have no fucking clue about female anatomy, so all I know is from strictly research)
> 
> -Corey

And that's how it went every morning and every night for that first week since he came and the first week of the semester. Cas would gather his clothes and change in the bathroom while Dean changed in their room. Dean was a little puzzled but waved it off as maybe the guy thought he was a little chubby or maybe too skinny?

Dean honestly didn't care. Dean didn't care how a person looked, he wanted them for what was inside. And maybe that's how Dean knew that he was bisexual a few years ago.

He noticed that Cas began to wear less baggy clothes. And boy, he thought Cas with fewer layers was a sight to behold. His shirts got smaller and his pants got tighter. God, Dean wished he could make a move.

It was late one night, that Saturday after their first week of classes. They were on the floor between their beds, several blankets creating a nest underneath them as they watched an animal documentary on Dean's laptop.

Dean was starting to zone out right before he felt a weight on his shoulder. He jerked his head to the left and realized that it was Cas's head. He had fallen asleep.

Dean took his time to follow Cas's features: his fluffy dark hair, his light stubble, and behind those closed eyelids were a bright blue light that Dean could drown in forever. His lips looked soft and plush, Dean couldn't help himself.

He closed the few inches between them and pressed his lips lightly to Cas's, moving them a few times, then breaking away with a sigh.

But he didn't make any noise. He glanced back at Cas, his eyes flickering underneath the lids, then opening. He opened them sleepily, then the instant they made contact with Dean's, they widened, and he scrambled back, his back hitting the side of his bed. He jumped up and curled in on himself on it. His breathing could be heard in the quiet silence of the room, the heaviness breaking Dean's heart.

"Shit, God, I am  _ so sorry,  _ Cas!" Dean cried. "I- I couldn't help myself- you just- just-"

"You- you can't kiss me! You can't- can't  _ like me _ ! I'm disgusting! I'm  _ gross! _ " He screamed.

Dean rushed to his feet. "Hey, hey, Cas. S'alright. I'm sorry. I- I didn't know that..." He broke off when he realized what Cas said. 'I'm disgusting. I'm  _ gross _ .' 

Before he could get a word out, Cas murmured quietly. "I don't have a prostate."

Dean blinked once. That might have been a bit of an overshare. But didn't all guys have one?

"Were you born without one?" Dean asked just as quietly as he kneeled in front of Cas on the floor.

"Yes," he said.

"Why do you think that matters, Cas? I don't care how someone looks-" Cas scoffed "-or anything. I kissed you because I like you."

Cas made a noise like he was going to say something before he sighed. He scooted to the middle of the bed. His hands caught the bottom of his sweatshirt and pulled it over his head. Under it, was a dark grey undershirt that he seemed to hesitate on, then nod and pull off. Under  _ that,  _ was this sort of tight undershirt that covered his chest.

Dean didn't know what he was looking at until he realized what it was. God, was this what Gabriel told him that Cas had to tell him on his own? Dean wanted to  _ cry.  _ He knew he had never met anyone that was trans, but he wanted Cas to know that he didn't care. He also knew that it was rude to ask questions like 'When did you know?', 'How hard is it to feel like the opposite of your assigned gender?', and 'Why did you not tell me?'

Pretty much everyone knew that the world had gotten better at accepting those who were trans. Medicine and therapy were more accessible, laws were passed that made it easier for them to legally change their name and gender with more leeway, and more people were learning why or how. But there were still lots of people who were different that got ridiculed.

He heard a soft sniffling noise coming from Cas. He was crying.

Dean leaped on the bed and gathered him into his arms. "Hey, shh. It's okay, Cas. I don't care. I really don't. You could have slimy fins, scaley skin, and webbed hands, and I'd still love you. Yeah, Cas. You heard me. I love you. I know it took a lot out of you to tell me this. I thank you so much for having your trust. Is this the only reason that you said we can't be together?" He skipped over the part where Cas said that he thought he was disgusting.

The longer Dean pet his head, it seemed that Cas calmed down more. He felt him swallow and take a deep breath.

"No one would ever love a monster like me," he whispered. "I don't have the courage to do surgery, so I just take pills. I don't like needles. So here I am, stuck with a body that's not mine. I mean, yeah, somedays I can deal with it more than others. It's only been recently that I feel that I can wear clothes and still pass."

Dean hummed, still petting Cas, sweeping his messy hair from his eyes. "I know this isn't going to help, but I'm saying it anyway. I'm bisexual. I don't care about someone's body. Cas, I love you for you. I hope that with time you'd feel more like you. I want you to be happy."

Cas shifted in Dean's arms to lay his head on Dean's shoulder. "I'm sorry for lying to you, Dean."

"Nah, Cas, don't be sorry. I know it must have been hard for you to tell me this. I just hope that we can get along better. If I could help you in any way, just tell me what you need, and I'll do it."

"Can you..." He trailed off.

"Can I what?" Dean asked.

In the dark, Dean could still see him blush. After a moment, he felt warmth on his thigh, slowly creeping upwards towards his cock. He gasped.

"I want to s- see it?"

Dean didn't have a problem with that, for sure. But...

"Why?" He had to ask. "Not that that's a problem," Dean rushed to add.

"I... I've never seen one before. And... I've always wanted one," he added rather shyly.

Dean was shocked. He's surely seen a bulge in Cas's pants every day, and he certainly felt something in them right now.

As if reading Dean's mind, Cas shifted away, leaning against the wall and pulling his pants down. He tugged them off at the feet to throw them on the floor with his shirts. Dean still saw it in his boxer-briefs. Cas hesitated for a moment, then nodded when he came to a decision. He gripped the sides, then yanked them down. And...

Dean's eyes were suddenly laser-focused on Cas's... not-dick. There was something on his thigh, but what Dean saw was the coarse, wiry hair where a dick should be. Instead, there was a... vagina.

Dean's eyes probably bugged out of his head, because Cas inhaled sharply as he curled in on himself. "I'm so sorry, Dean. I- I..."

Dean leaned forwards and smashed his lips into Cas's, his hand coming to cup the back of his head. They broke apart gasping.

"I don't care what parts ya got, baby. You say you're a guy, you're a guy. And if you're okay with it, I want to make you feel good. I want you to see who I see you as." There stood a question in Cas's eyes. "I see you as a brilliant being: kind, caring, happy, smart, fascinating, funny, and the overall best man I've ever met." He licked his lips once. "And, uh... if you want me to, can I take off my clothes so you're not the only one naked?"

Cas nodded, and Dean began to strip, not an ounce nervous, doing this to show Cas that he loved him. That he could be loved. 

When he was naked, he sat back down on Cas's bed, feeling a bit jittery and nervous when Cas stared at his dick, his hands making a small, grasping motion like he wanted to touch him.

Dean cupped Cas's right hand and brought it slowly to his crotch. When his skin met Dean's, he whimpered a bit, then started to move his hand up and around it, getting a feel of it. He curled his hand on the bottom of it and picked it up, getting a test on its weight. Dean tried his damndest not to get too aroused; this was a moment for Cas. Cas needed to feel assured. He was also curious.

Cas's hand eventually wandered up his shaft and to his balls. And yeah, Dean was already getting sexy vibes.

Before Dean could stop himself, he gasped, "Can I touch you too, Cas?"

Cas stopped his movements, and Dean was about to step back and say sorry again, but Cas looked at Dean with... could it be love?

Cas licked his lips, his pink tongue swiping between them. "You, uh... you actually want to  _ touch  _ me? In- in  _ that way _ ?" He seemed that he was amazed if Dean was telling the truth.

"Yeah, baby. You're over here feeling me up. And yeah, I know that you probably didn't think it was sexual, but it's kinda turning into that."

Cas took his hand back then said, "If... if you want to, I think it would be alright. Over the years after learning that I was... different-"

"Trans," Dean interrupted with a smile. 

"-That I was...  _ trans,  _ I started to take pills for my testosterone- which, uh..." Cas paused, then started again. "When I hit puberty, which, ugh, just thinking about it makes me want to vomit- I had awful cramps, hating that one week when I felt most vulnerable, bleeding my guts out and that was just my body's way of telling me that I wasn't supposed to be that way. Anyway, I knew all the outcomes when Gabe took me to different doctors.

"My parents..." Cas sighed. "My parents would dress me up in the designer dresses, braid my  _ perfect, long, wavy hair _ ," he mocked. "When I was nine or so I began to fight them- both signs of having autism and being trans. Most of the time, I was fine with it. But some days, I would get so angry that I clawed at my chest, hoping and praying that the stupid, lumps of fat would just  _ go away _ . Gabriel, of course, saw the signs and asked me if I wanted to get my hair cut.

"And Dean, when I did, it was like a weight being lifted. I would look in the mirror and say, 'You're doing good, Castiel. You're one step closer.' That day when our parents came home, they screamed more at me than Gabe. I never really loved them. They threw their money at me and that's how they said 'fuck you'. They were more than willing to sign the papers to hand me over to Gabe. We moved from Boston to League City. He took me to so many doctors to help me.

"One of the first ones was a gynecologist. And that's when we figured out I had polycystic ovary syndrome, otherwise known as or PCOS. She told me the symptoms which were along the lines of heavy periods, terrible acne, being overweight or underweight, and most of all- and don't be surprised on this- excess testosterone. Which is what can cause me to be trans! So, tell those to the assholes who say there's no science behind it.

"She sent me to other doctors, too. After a few months, we decided to start me on HRT. And Dean, that made me so happy. I wanted my estrogen  _ gone. _ " He paused. "So that's what happened the next few years. It was a good thing that I started it young enough, so I was able to go through speech therapy and all of that. 

"After a while, it got better to deal with my body image. I got skinnier, more muscles started to build up, I grew more facial hair, for goodness sake!" After a few moments, he said, "I attended high school. And that first year was..."

"Not that great?" Dean asked quietly, kind of knowing that after a year or so HRT would probably not do that much.

"Yeah," Cas blew out a breath. "I didn't pass all that well. The guys made fun of a girl who wanted to be one of them, calling me awful slurs that I dare not repeat. And the girls... I don't think they really understood? I don't know if anyone could have put themselves in my place. No one ever really tried, you know?" He swallowed then moved on.

"Eventually, I was able to get my gender changed. That day was..." He shook his head in disbelief. "Fantastic. I applied to college as a male. I went to the men's bathrooms. And now I can even pass as one. But, I still can't think about changing my body with top or bottom surgery. It's..."

"Scary?"

"Yes."

"I think you've gotten through an amazing amount of things, with such great effort and dedication. And I don't love you any less." Dean kissed the top of his forehead.

"I'm sorry for killing your boner with my kicked-puppy story," Cas mumbled.

"Nah, it's your hero's tale," Dean smirked as he pushed Cas down on to his bed, pulling off his binder and tossing it with the rest of their clothes. Just then, he felt something nudge his hip. "Cas, I thought you said, and-" He paused when he finally saw what it was.

He blinked once. "Wha's-"

"Oh, uhm... it's a kind of, uh, prosthetic, I guess? Also multipurpose as a packer, and a-" His blush was getting so bad that Dean wanted to laugh with happiness.

"S'it also what you use to pee with?" Dean asked.

"Uh, yeah?" He coughed nervously. "I'm sorry, Dean. It might be just a tad bit weird for me to finally have a boyfriend and him being so understanding and-"

"I'm your boyfriend?" Dean smiled softly after pecking him on the lips once.

"If that's alright with you-"

Dean collapsed on top of him, not at all minding his breasts, needing to hug the shit out of him. "I'd love to be your boyfriend, baby."

Cas squealed for a moment before stopping himself. He cleared his throat. "Sorry."

"Nah, s'fine, Cas." Dean thought of what to say for a minute. He licked his lips and swallowed. "Are you... are you alright if I wanted to, uh... touch you there? I mean, it's okay if you're not! I just, ah. The more we talked, the more I wanted to meet you. And when I saw you," Dean blew out a breath. "When I saw you, I wanted to kiss you and... make love to you. I know that was before you told me this, but I'm still willing to do anything I can to show you that I want to be with you no matter what. Gah, I'm sorry for talking so much. I just want you to-"

Dean didn't have a chance to finish his ramblings because Cas hooked his arms and legs around Dean to pull their mouths together in a bruising kiss. Cas opened his mouth to prod his tongue at Dean's while gently rolling his hips against his boyfriend's.

They pulled away short of breath with a string of saliva connecting their lips to one another's. Their gazes met and held as they stared at each other with love.

"Yes, Dean. It's totally fine with me. Although, I might have to warn you that with the medications, they make my chest and genitals more sensitive. So, uh- can we take it easy? That is if I'm getting the right messages from you that you want to have sex with me?"

Dean chuckled, saying, "Well, now that we have no secrets between us, I gotta ask one more thing. It's also a necessity." Cas nodded. "Can you get pregnant?"

Cas's eyes widened. "There might always be a chance of it until if I get my ovaries removed? So, if that's your way of asking if you need a condom, I'll say 'yes'."

Dean smirked quickly, then rushed to his drawers and dig around until he found the box buried under socks and underwear. He ripped one from the others and brought it back to Cas's bed and sat beside him.

They stared dreamily at each other until Cas broke it to look down at the bed between them. "I've never had sex before, Dean," he confessed.

"Yeah, me neither. Another thing, which way do you want it? Like, through the front or the back?" Shit, he was blushing so much that he felt like his face was on fire. But this was a good thing; he was finally getting somewhere with Cas. "And, Cas, just because you're gay doesn't mean that you have to like it up the ass, by the way. Just tell me what you want, and we can go from there?"

Cas shifted a bit, maybe he might've been uncomfortable? When he didn't respond, Dean asked, "How about we try and we can see what you like best?" Dean waited a moment, then when he got a nod from Cas, Dean set the condom on Cas's bedside table.

"Okay, Cas, can you lay down, set your head on the pillow?" Cas did as Dean said, so he moved on, slowly taking in Cas's naked form in his bed. His breasts were maybe a B-size, they got more flat as he straightened himself. His stomach was flat but still soft in some places. Below his belly button was a trail of soft hairs that grew thicker and darker as it led to his crotch. The thatch of hairs covered the area, but they were neatly trimmed and kept. His legs-  _ god, those thighs-  _ were dusted with short hairs, just as dark as the ones on his head. His whole body was muscular in a beautiful way that Dean loved even more about him.

Cas ducked his head, his face beet-red. "You're staring, Dean."

"Oh, uh, sorry, baby. You're just so... beautiful. Oh, wait, do you want me to use more masculine terms or-"

Cas leaned up and pressed his lips softly to Dean's. "It's okay, Dean. You're beautiful, too. But, I  _ might  _ prefer a bit more masculine terms. If you want to call me pretty or beautiful, you may do so however much you want."

Dean smiled at that, proud of having Cas's permission. He pushed Cas back down. "Okay, Cas. I think I might have an idea of something you might like?"

"Okay?" Cas said curiously with some caution.

Having that as his permission, he leaned back and slowly pushed Cas's legs apart. He heard Cas's breathing get heavier.

Dean looked at him from where his head was by his stomach. "Hey, hey, baby, shh. S'alright. S'okay. Uhm, how about I tell you what I'm going to do before I do it so you have some warning and you know what to expect?"

Cas nodded, clearly his speech was gone.

"So, what I was hoping to do was... I might have read what both girls and guys like a few years ago. Never had to use the knowledge until now, but ah, apparently lots of people like to be licked... down... there. It seems that it's probably the most sensitive of areas on the human body."

Cas gasped and started to nod frantically. "Yes, Dean. Yes, yes,  _ yes _ ."

Dean smiled softly, then he pushed Cas's thighs up and out, Dean's face now level with his crotch. Dean took an inhale by accident and realized that he smelled like... fruit? Okay, yeah, Dean's seen the body wash in their shower. Dean had his beach stuff while Cas had his apple and pear stuff.

Dean took a breath, then used both his hands to part Cas's lips, pulling them apart to get a good look at the most private part of Cas, to see it soft and squishy, some of his juices making it wet and ready for Dean. After a moment of hesitation, Dean closed the inch between them and stuck out his tongue to lick the top of him. He smiled when he heard Cas gasp. He moved on to press his tongue at the bottom, using the muscle to swipe up his vulva and back to the top. Then he swirled it around, gathering up his juices and swallowing it down, not at all minding his taste. Cas's thighs twitched when Dean found his clit and began to pay more attention to it and suck around it. 

"D- Dean,  _ Dean, oh God _ ," Cas started to blubber nonsense while Dean heard tears in his voice. "Oh my, I love you so much, Dean.  _ So much _ !" He gasped and screamed when Dean nibbled a bit. "Ahhh,  _ Dean _ ." 

At that, Dean stopped because he didn't get to the best part yet. He wanted him and Cas to be there together when they came. Dean pulled his head back, letting go of Cas and telling him to relax his legs. Cas dropped them and sighed.

"I... I didn't even know that it would feel so good," he whispered. He pulled Dean on top of him and pushed his tongue into Dean's mouth, the two pink, wet muscles dancing with each other. They pushed and pulled, twining together and mixing their spit. When they broke apart, Cas's eyes were full of stardust, twinkling when they made contact with Dean's.

"I love you, Dean," he whispered.

"I love you too, Cas," Dean smiled and said just as quietly.

When he began to pull away, he felt Cas's warm hand touch his dick and pull it towards his opening.

"Hey, hey, hey, Cas. No, remember I gotta put a condom on?" Cas legit  _ growled. _ "Yeah, I know it sucks. I just don't wanna tell my parents that I got my boyfriend pregnant. Not in college, baby. If you want to someday, we can talk about it, but we're paying  _ a hundred and twenty THOUSAND DOLLARS  _ to come here. And I don't think either of us could deal with taking care of a child while balancing school work. And also, STIs? Do you want one?" Cas stubbornly shook his head while Dean realized how stupid he was with what he just said. "Well then, it's settled. Maybe later, we can figure out if you like it up the ass, too?" He smirked when Cas practically buzzed.

Dean hummed once before he grabbed the condom and tore the package open, throwing that on the floor while he rolled it on his shaft. When it was on good, he leaned over Cas, one hand by his head and the other holding the base of his dick to guide it to Cas.

"You ready, Cas?" He asked shyly. Cas whispered a calm 'yes'.

Dean kissed him once, then brought his cock to rest between Cas's lips, then sunk in at once, slowly rolling his hips until he was flush against Cas's. Cas looked down to where they were connected, then back up to Dean. They both giggled at the same time, packed with joy with what they were finally doing.

"God, I can't believe that we're the ones to laugh during sex," Dean groaned. "I mean, it's great that we can just let loose and have fun, but..."

"Is it weird?" Cas asked worriedly. "Is it weird that you're  _ inside  _ of me? When you thought I was a guy-"

"Because you are," Dean interrupted.

"Yeah, but... is it weird to you that you're having s- sex with me. In my va- vagi-" Cas couldn't even finish before he broke down crying.

Dean didn't bother pulling out, his erection tucked in nicely where it belonged. He just leaned down on his left near the wall and pulled Cas closer to him, still connected together. He pulled Cas's leg over his thigh and rested his chin on the top of Cas's head.

And so they lay together for a long time, Cas cried and sobbed while grasping to Dean like a lifeline, Dean petting his short, ruffled hair and shushing him.

When he seemed to calm down, Dean took a breath. "I know that I will never fully understand what you have gone or are going through. Please do not push me away when it gets bad. I want to help you in any way I can. If I held the power to change you into a man with a flat chest and a real dick, I would do it just to see you smile again. I would go through Hell to make sure no one ever teased you again. I would come sit by you in the bathroom when you're vomiting and pull your hair back and tell you how handsome I think you are. I would tell you I love you when you're at your end, to tell you to take a breath and think about our future. To tell you all my plans for our future.

"I would tell you I love you when we take that trip to NASA. I would tell you I love you when we go to your house and spend days in your bed doing whatever the hell we wanted. I would tell my parents that I love Castiel, the smartest man I've ever known, that I'm willing to do whatever it takes to earn all his trust. I would tell Gabriel that I love Castiel, the most loving man I've ever known, as I ask for his blessing with a ring just as beautiful as the love of my life. I would tell Castiel, the kindest, sweetest man I've ever known, that I love him as I get down on one knee and ask him the question of my life. I would tell you, Castiel James Novak, that I will never let you go no matter what when we exchange rings at our wedding, moving on to the next stage of our lives."

He was openly crying when he sobbed out, "And I will spend my eternity in Heaven loving the only man I've ever wanted. I love you, Cas. And I want to show you how much I love you for as long as you'll have me."

He felt Cas's hands come up to his cheeks and wipe at his tears, placing soft lips on Dean's. He pulled away to look at Dean. "I honestly have no idea what to say. I am, so to say, speechless. You've taken your time to make me comfortable in this space and show me that you do care for me- even when no one else has. If that was your proposal, I would say yes now, and I'll say it every time when you tell me to keep trying. I'll try, and I'll succeed because I have Gabe. And I have you, my love."

Dean opened his mouth to say something, but it came out as a whine when he felt Cas shift on his dick, both of them being reminded of what they were doing. Cas pushed Dean onto his back and climbed on top of him, his breasts swaying a little from side to side. Dean held on to Cas's hips while he started to move in figure-eights, eventually putting both his palms flat on either side of Dean and began to rock back and forth, humping him in a steady, sensual pace.

They both gasped and groaned when the tip of Dean's dick hit the deepest part inside of Cas. The two of them created a frantic pace while rocking and thrusting, both of them in their own world, only focused on the other. Dean pushed himself up, his mouth becoming eye-level with Cas's chest. He flicked his eyes up to ask Cas if it was okay, and Cas looked back down at him with pure adoration in his eyes. He nodded. Dean opened his jaw to mouth around the rise of Cas's chest, his lips coming to rest on his left breast. He poked out his tongue and gave the nipple a little lick, drawing a sharp gasp from Cas. He began to suckle on it, alternating between the left and the right to give them equal attention. 

While Dean licked and nipped at Cas's breasts, Cas moved for both of them, thrusting up and down to create friction. Dean bit a little too hard around his right breast, feeling Cas lock up and scream. Dean was about to ask if he was alright before he felt Cas's folds tighten around him, squeezing around his dick, causing Dean to moan while they both came at the same time.

Dean felt wetness on his shoulder, and he pulled back to see what was wrong, Cas's eyes swimming in tears.

"Hey, hey, shh, Cas," he soothed while rubbing Cas's back. He leaned back while pulling Cas on top of him. "Baby, you alright?"

Cas inhaled and sniffled. "I... it felt  _ so good _ , Dean," he mumbled into Dean's neck, warm puffs of air causing his skin to prickle in that spot. "All my life, I felt that this body was cursed. I hated that I could never be a true man. But, even though we didn't have sex how I wanted to, you still showed me that I'm n- not  _ cursed _ . I can still be me- still feel the way I do- and still-"

"Have sexy fun times?" Dean smirked, causing both of them to chuckle. Dean told him that he needed to take care of the condom, so they both got up, Dean going to the trash and Cas going to the bathroom. When Dean was done, he wandered to the door of the bathroom, which was still cracked open. He opened it more, and his eyes fell on Cas, his perfect ass bent over.

"Whatcha doin'," Dean asked. Startling, Cas jerked up like a frightened cat, turning more to the corner and away from Dean. "Hey, no. Cas, remember, let's be open about things? I'm sorry for scaring you."

Cas turned around to face Dean reluctantly, some sort of baby wipe in his hand. "I... I'm too lazy to take another shower, so I'm just..." He stuttered through his excuse.

"You need to be cleaner, so you're using wipes?"

"Yes! Exactly! I..."

"Cas," Dean chastised. "I want you to know that you can tell me anything. The first night I wanted to tell you that we were both guys, and I wanted to share everything we wanted to with each other. I know that might have made you more closed-off, but I'm telling you now that even though we ain't got the same parts, we're both guys. And like you said, there's science in it. And that's something I can believe in." He looked back into the small hallway at the entrance of their dorm then back at Cas. "I'll let you clean up, I'll find you some clothes. Any preferences?'

Cas fidgeted a bit, then said, "I uh, I usually wait for you to fall asleep before changing into real pajamas. I'm not supposed to wear a binder for an extended amount of time, so I have sports bras and other, uhm... comfier ones? During the night, all I have is one of those, a shirt, some underwear, and shorts or pants. For the underwear, it's kind of the same thing, too. I have some that were made with packers in them. I mainly use those ones on a daily basis. I have boxer-briefs that I use for the uh... could be called a dildo," he smirked, making Dean chuckle. "I still have some leftover ones from when I was beginning the HRT and are called 'boy shorts'," he said with finger quotes. "I could explain more later if you would like. And uh, I have very few of them, but they're basically girls' underwear. I still don't know why I have those. Maybe some attachment or something."

Dean shot him two finger guns and said, "Alright, I'm on it. You finish up in here and I'll go get what I think you'd like best."

He closed the door to give the man some privacy. Wandering to Cas's drawers where he thought his stuff might be, he opened the top one first. That was full of odds and ends, shirts, and shorts. He knew the bottom one contained pants and socks. He pulled open the middle one, whispering 'bingo' when he found it packed with several different kinds of underwear, bras, and binders.

He picked up the first pair of tight boxer-type underwear, knowing that these were the ones that when Cas wore them made his crotch have a bulge to them. There were three or so pairs of those from dark grey to light blue. The next thing he found was two pairs of regular boxer briefs, with the slit and all, one black and one red. He found three pairs of underwear that seemed like very short shorts, the material stretchy, and the colors of two white and one light blue. In the back of the neat pile were these two lacey things, and as Dean's fingers ran over the material, he felt a spark in him and jerked his hand back, grabbing the pair of white boy short ones, thinking that those would make Cas feel comfier.

He glanced over the two binders, one white and the other black. Dean looked back to the grey one on the floor then back at the other ones.

Dean turned his attention to the about half-a-dozen bras. Half of those were what seemed like the 'sports' ones. Dean quirked a small smile, this would be his first time actually touching a  _ bra _ . 

Man, he was eighteen and he just had sex for the first time. He still couldn't believe that he and his best friend were dating now!

Moving to look at the others, he blinked once, his jaw falling to the floor. Those ones looked like the comfy ones Cas was talking about; they looked like something from  _ Victoria's Secret _ , really. They had adjustable straps, lace, and a soft, stretchy material. He wondered whether Cas would like the sports ones or the regular ones better? It seemed that Cas trusted him enough to make the decision for him.

But what if he screwed up? What if he gave him the opposite of what he wanted.

He decided to grab a white one of each, holding those and the pair of underwear in his left hand. Dean went over to his side and quickly grabbed a soft t-shirt for Cas, too.

He knocked on the door and opened it, walking in to see Cas trying to brush his hair, not at all succeeding in the task. Dean's face softened. He put the clothes down on the edge of the sink and turned to Cas. He took the brush out of his hand to set it on the shelf with his other things and gathered Cas close, just now remembering that they were both naked as the day they were born.

Dean smooched Cas on the lips once. "Got you some things to change into for bed. S'almost midnight and I want to spend some more time with you tomorrow until classes start again."

Cas turned to the sink and saw what Dean got for him. "Why did you get me two?" He asked curiously, tilting his head in that goddamn adorable way.

"I uh, I didn't know which you'd like better? I thought that this one," he held up the looser bra, "might be more comfortable for you. But I thought this one," he pointed to the sports bra, "might make you feel more compact? So I just took both to ask your opinion."

While Dean was talking, Cas picked up the underwear and stepped into them one leg at a time. When the elastic snapped on his hips, he looked back up at Dean. "Well, everything I own does mean that I wear all of it- just sometimes not as much as others. The tighter my undergarments are on me, the more dysphoric I am. That also means that my outer layers will be baggier and looser. Other days, when I'm not as sick, I can wear mainly whatever I want. And since I'm wearing a shirt tonight, I could just put on the regular one." When he finished talking, he picked up the bra that wasn't the sports one and put an arm through each strap, laying them on his shoulders. He made an impressive move by folding his arms behind him to hook the part behind him, making himself look like a contortionist. After he did that, he positioned the straps to where he wanted to, then picked up the shirt. He was about to put it on before he paused.

He looked down at the  _ Marvel's Avengers _ logo and smirked. "You want me to wear your shirt?"

Dean blushed and coughed once. "I mean if that's alright with you? I was... I was hoping that maybe we could sleep together?"

Cas's mouth quirked up in the cute, gummy smile that Dean just had to kiss right off. Cas moved his lips a few times against his before breaking apart. "Yes, Dean, that is totally alright with me," he said breathlessly, put the shirt over his head then followed Dean back to their room. Dean tossed his pajamas that got torn off in haste to the side by his bed. He only took his boxers and pulled those on, hopping under the covers next to Cas. He held his arms in an open invitation for Cas to snuggle up next to him.

And Cas did. He curled his arms around Dean's torso, tucking his chin under Dean's. Dean put an arm around Cas's shoulders, the other resting on Cas's stomach. They drifted off together in warmth and happiness.

**Notes for the Chapter:**

> There might be more than a week (maybe a month) until I have the whole next chapter written. I'll do my best.

**Author's Note:**

> Thank you for reading and please check back in the next (should I say month or year (I'm trying, okay?)) foreseeable time for more Destiel fics!


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